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Advise on our itinerary

We are staying with friends in Florence and Cinque Terrre in early October (5 or 6 nights)
When we leave them in Florence we are considering the following:
Rent car in Florence and leave in morning heading to Siena stopping along way in San Gimignano. Overnight in Siena and leave in morning heading to Orvietto. Stop along the way in Montalcino, Montpulcino, Pienza (any or all of the 3). Stay in Orvietto 2 nights before driving to Rome, stay 1 night close to airport to return car and our return flight.
Any recommendations on any of these towns or any others that would be good?
Has anyone stayed outside of Orvietto in a farm B&B? If so, is it recommended to do that and just drive to see Orvietto. Can we park the car and take the tram up? If we stay in the town instead, what about parking?
We had a brief stop years ago in Siena on a tour we were on so do not need long stay there and we have also done Rome.
Your input on our plans or any other recommendations will be much appreciated.

Posted by
872 posts

It is a very bad idea to leave anything of value in a car when parked. The best procedure is to head directly to a hotel and drop off bags before doing any sightseeing.

Regarding FCO, the Hotel Tiber on the waterfront in Fiumicino is a comfortable place to stay, good restaurants nearby.

Posted by
149 posts

I’d suggest focusing on one/two of Montalcino, Pienza, and Montepulciano rather than trying to see them all and drive to Orvieto on the same day. That would be a whirlwind and you’d get to Orvieto quite late in the day.

Pienza is quite small (and flat) and you could see it in a couple hours so it can work well with another stop. Montalcino is larger, and Montepulciano is the largest with the most to see and do and was the busiest on our visit. I enjoyed Pienza for the ambiance, and the lesser crowds. Montalcino was also not so busy.

If you’re into wine there are excellent wineries in the countryside and also in Montepulciano proper.